1-Chloro-4-nitrobenzene → 1-Methyl-4-(4-nitrophenoxy)-3,5-diphenyl-1H-pyrazole

HRID 1658396Notes

Reaction equation

[OH:1][C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:4][N:5]([CH3:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].Cl[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1.[OH-].[Na+]>O.CN(C=O)C>[CH3:13][N:5]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]([O:1][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[C:3]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[N:4]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 4-hydroxy-1-methyl-3,5-diphenylpyrazole (10 g, 0.04 mole), potassium t-butoxide (4.5, 0.04 mole) and dry DMF (150 ml) is stirred and heated to 60°C. The green fluorescent solution is cooled to room temperature and p-chloronitrobenzene (6.0 g, 0.038 mole) is added. The dark green solution is heated at 60°C for 24 hours and then poured into water, made alkaline with 1N sodium hydroxide and extracted with ether. The ether layer is separated, washed well with water, dried and stripped in vacuo to give a bright-yellow solid 12.9 g (86.5%), m.p. 85° to 110°C. The solid is chromatographed on silica gel with benzene to give a yellow crystalline solid 11.3 g, m.p. 74° to 100°C. Recrystallization from methanol (185 ml) affords white crystals 5.5 g (37%) m.p. 120° to 122°C.

Workup

temperatureThe green fluorescent solution is cooled to room temperature
temperatureThe dark green solution is heated at 60°C for 24 hours
extractionextracted with ether
customThe ether layer is separated
washwashed well with water
customdried

Sources & evidence

ORD record: ord-227e207735984cf0ada0d5195befb0b9
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03963742

Reaction notes

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